Jared opens Mailbag Monday from Delray with gratitude, beach energy, and a reminder that anonymous advice hits harder than biased friends. The standout email comes from a listener who went on six “pretty good” dates and can’t stop thinking about bunny-rabbit sex, being asked to fetch latkes, and having to share a single hot dog at a hockey game. Jared’s verdict is clear and funny: if it’s still only “pretty good” after six dates, that’s already your answer. He reframes dating like investing, asking whether this relationship could realistically get 10 percent better and become a life you actually want. The lesson is not that she’s too picky, but that chemistry matters more than politeness and settling only builds resentment. Classic JTrain delivers a warm hug, a reality check, and permission to move on without guilt!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Get $2.99 per meal on your first box & free steak for a month with code JTRAINSTEAK at http://everyplate.com/podcast  

Pop Culture Thursday has Jared breaking down Ashley Tisdale opening up about toxic mom groups and why it hits home for millennial women. He also gets into Amy Schumer’s Instagram post during her divorce and what it says about body image and fame. Plus, Cher weighs in on Kristen Bell and Dax Shepard, and why trips to St. Barts make celebrity drama even louder!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Find and cancel your unwanted subscriptions with Rocket Money at https://www.rocketmoney.com/JTRAIN 

Eat smart @ http://factormeals.com/jtrain50off & use code jtrain50off to get 50% off your first box, plus Free Breakfast for 1 year.

Jared kicks off Chit Chat Wednesday in Delray with John Gabrus, and they immediately “break up” as friends because Jared moved to Florida without telling him. They bond over midlife “why didn’t I just live near a beach?” energy, then detour into comedy-world gripes, including how movies love stunt casting when there are a thousand actual funny comics available. Gabrus shares his peak midlife-crisis triumph: a solo Mexico trip for surfing and intensive Spanish classes to get off his phone and feel alive again. They then end by playing a Hillstone menu game that reveals Jared is Team Girl Lunch while Gabrus is Team Steakhouse Dad. They promise to finally hang out, which in podcast terms means it might happen sometime before the next Ice Age.

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Find and cancel your unwanted subscriptions with Rocket Money at https://www.rocketmoney.com/JTRAIN 

Eat smart @ http://factormeals.com/jtrain50off & use code jtrain50off to get 50% off your first box, plus Free Breakfast for 1 year.

Jared opens Ticked Off Tuesday from Delray and immediately roasts himself for showing up to “the hottest restaurant in Delray” on Christmas Eve…only to realize his reservation was for January 1, 2026. He then spirals into beach-walk social awkwardness and floppy-hat groups refusing to go single file. The big vent is Delta, where he claims the airline hides his hard-earned upgrades in the app like a toxic partner gaslighting him about their “benefits.” Listener complaints bring the chaos: a hungover flyer forced to watch a seatmate bite and display nail clippings like tiny trophies, a university worker exhausted by parents doing adult kids’ basic tasks, and a mother-in-law who treats dinner parties like an HGTV intervention. Overall, petty grievances, Florida sunshine, and Jared turning everyday annoyances into a full-on comedy sport!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the show and get $10 off your 1 st month of Nutrafol with code FEATHER at https://www.nutrafol.com 

Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co

Jared kicks off the real first Monday of 2026 with Mailbag Monday energy, reminding listeners that resolutions start now and inviting everyone to put their brain on the shelf. The first email comes from a self-proclaimed “classy” guy spiraling over a friend’s engagement ring he finds tacky, and Jared’s advice is simple: if no one asked for feedback, keep it to yourself. Next, a listener admits she’s stuck in a two-year-long-distance situation with a man who has never wanted commitment, while dating a “nice and consistent” guy she feels less excited about, and Jared delivers tough love that she’s chasing vacation-mode potential, not a real relationship. Finally, a listener feels awkward chasing friends for Venmo pizza money. 

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the show and get $10 off your 1 st month of Nutrafol with code FEATHER at https://www.nutrafol.com 

Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co 

Jared kicks off the New Year by breaking down celebrity headlines of the week! From Jeff Bezos allegedly commissioning a statue of Lauren Sanchez to Brooks Nader turning a belt into a top, Jared unpacks the absurdity of wealth, beauty standards, and attention economics. He also calls out Elizabeth Hurley’s unrealistic bikini “tips,” dives into Cardi B’s clapbacks, and dissects how Page Six fills slow news weeks. A smart, funny look at celebrity PR strategies, critical thinking, and why pop culture is still so entertaining!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Jared kicks off Chit Chat Wednesday with comedian Caitlin Peluffo, joking about her life as a road warrior and the reality of touring, from romanticizing small towns to surviving bleak winter clubs on comedy club coffee. Caitlin gives a Hallmark-level rundown of her parents’ over-the-top 55+ community Christmas setup, complete with gingerbread villages, reindeer plaques, and stockings with old-school oranges. She also shares why being single is her current glow-up: no emotional management, no long-distance stress, just peace, vibes, and group chats. They wrap with a goofy round of “Flabby or Fab,” shout out to Caitlin’s upcoming shows, and agree that a Zingerman’s sandwich in Ann Arbor is non-negotiable!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Ticked Off Tuesday kicks off with Jared roasting the podcasts that “took the week off,” declaring Best Of episodes basically a slap in the face when everyone needs comfort-content most. Then he vents about the Paul brothers making an absurd $92 million boxing a pro. His main chaos story is an Orlando show where late arrivals spent eight full minutes loudly ordering drinks  mid-set. Listener rants pile on: speakerphone calls on a 7am NYC train, a beloved best friend whose “maximalism” has become full trash ecosystem, and a budget massage place that tried to demand a $20 tip like it was an entry fee. He closes with a very millennial-sounding housing/internet nightmare that turns into a realization: we are forever the test generation, getting whiplash from “your building only has AT&T” to “lol it’s all in the air now.”

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co 

Support the show and get $10 off your 1 st month of Nutrafol with code FEATHER at https://www.nutrafol.com

Mailbag Monday lands in the weird, snack-filled limbo between Christmas and New Year’s, and Jared proudly reminds you that while other podcasts are “resting,” Uncle J Train is still clocking in. He tackles a Hallmark-level dilemma about crushing on a cute, ring-free optometrist and how to shoot your shot without turning it into a LinkedIn crime scene. Then he breaks down the “fifth date shut down” question and why silence afterward can actually be a helpful answer for both people. The episode takes a surprisingly sweet turn with a one-year-later follow-up from a listener who finally said “I love you” after a divorce—and it worked—sending Jared into full sentimental mode. It’s equal parts dating advice, gentle pep talk, and holiday-season camaraderie.

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Support the show & get 10% off your Hero Bread order with code FEATHER at https://www.hero.co 

Support the show and get $10 off your 1 st month of Nutrafol with code FEATHER at https://www.nutrafol.com

On this special episode of the JTrain Podcast, Jared Freid breaks down the week in pop culture, from Brooklyn Beckham’s family drama to Jennifer Lopez and Ben Affleck’s headline-making relationship, plus updates on Tom Brady and Gisele Bündchen. The conversation also hits celebrity love lives and media scrutiny surrounding Ariana Grande, Amy Schumer, Lily Allen, and influencer culture through Alix Earle. With sharp humor and honest takes, Jared explores how fame, social media, and public opinion complicate relationships, whether you’re a global superstar or just living online!

Jared is on tour! 👉 jaredfreid.com

Check out his new book! 👉 Preorder Walking Red Flag: Dating Advice from Your Favorite Guy Friend

Find and cancel your unwanted subscriptions with Rocket Money at https://www.rocketmoney.com/JTRAIN